Potassium Phosphate, Tribasic → Diketopyrrolopyrrole

HRID 2209323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2209323
BrC1C(=O)N(CCCCCC)C2C=1C=C1C(=C(Br)C(=[O:20])N1CCCCCC)C=2.C(C(CCCCCCCCCC)C[N:39]1[C:46](C2SC(B3OC(C)(C)C(C)(C)O3)=CC=2)=[C:45]2[C:41](=[C:42](C3SC(B4OC(C)(C)C(C)(C)O4)=CC=3)[N:43](CC(CCCCCCCC)CCCCCCCCCC)[C:44]2=[O:61])[C:40]1=O)CCCCCCC.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1.O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.CO>[O:20]=[C:45]1[C:46]2[C:42]([CH:41]=[CH:40][N:39]=2)=[N:43][C:44]1=[O:61]

Komponenten

8

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 22272177Toluene waterHCID 866982713,7-dibromo-1,5-dihexyl-1H,5H-pyrrolo[2,3-f]indole-2,6-dioneHCID 866982722,5-Bis(2-octyldodecyl)-3,6-bis(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione

Produkt 1

HCID 23363597DiketopyrrolopyrroleAusbeute 655,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 2734635Tri-tert-butylphosphine tetrafluoroborateKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 3,7-dibromo-1,5-dihexyl-1H,5H-pyrrolo[2,3-f]indole-2,6-dione (0.075 g, 0.148 mmol), 2,5-dihydro-2,5-bis(2-octyldodecyl)-3,6-bis[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thienyl]-pyrrolo[3,4-c]pyrrole-1,4-dione (0.168 g, 0.150 mmol), Pd2(dba)3 (4.0 mg), tri-tert-butylphosphonium tetrafluoroborate (2.0 mg), K3PO4 (0.095 g) and toluene/H2O (8 mL/0.5 mL) was heated at reflux for 48 h. Then after cooling to room temperature, the mixture was dropped into methanol to precipitate. After being filtered and dried, the precipitation was Soxhlet extracted with methanol, acetone, hexane, dichloromethane and chloroform in succession. The chloroform solution was concentrated and reprecipitated in methanol. The solid was filtered and dried to yield polymer (0.130 g, 72.6%) as a black solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 48 h
  3. customto precipitate
  4. filtrationAfter being filtered
  5. customdried
  6. customthe precipitation
  7. extractionextracted with methanol, acetone, hexane, dichloromethane and chloroform in succession
  8. concentrationThe chloroform solution was concentrated
  9. customreprecipitated in methanol
  10. filtrationThe solid was filtered
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d2b0ddf35b62419fbba365b5389431d6
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09379335B2

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